2-((2R,3R,4R,5S)-4,5-Bis-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-ylmethyl)-2-tert-butoxycarbonylamino-malonic acid diethyl ester

Base Information

Chemical Name:2-((2R,3R,4R,5S)-4,5-Bis-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-ylmethyl)-2-tert-butoxycarbonylamino-malonic acid diethyl ester
CAS No.:869194-07-0
Molecular Formula:C₃₃H₄₅NO₁₂S
Molecular Weight:679.786
Hs Code.:

2-((2R,3R,4R,5S)-4,5-Bis-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-ylmethyl)-2-tert-butoxycarbonylamino-malonic acid diethyl ester

Synonyms:2-((2R,3R,4R,5S)-4,5-Bis-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-ylmethyl)-2-tert-butoxycarbonylamino-malonic acid diethyl ester

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Chemical Property of 2-((2R,3R,4R,5S)-4,5-Bis-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-ylmethyl)-2-tert-butoxycarbonylamino-malonic acid diethyl ester

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Technology Process of 2-((2R,3R,4R,5S)-4,5-Bis-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-ylmethyl)-2-tert-butoxycarbonylamino-malonic acid diethyl ester

There total 5 articles about 2-((2R,3R,4R,5S)-4,5-Bis-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-ylmethyl)-2-tert-butoxycarbonylamino-malonic acid diethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.0%

: 869194-04-7
1,5-anhydro-2,3-di-O-benzyl-6-bromo-4-O-(methylsulfonyl)-D-glucitol

: 102831-44-7
diethyl tert-butoxycarbonylaminomalonate

: 869194-07-0
2-((2R,3R,4R,5S)-4,5-Bis-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-ylmethyl)-2-tert-butoxycarbonylamino-malonic acid diethyl ester

Guidance literature:: diethyl tert-butoxycarbonylaminomalonate; With sodium hydride; In toluene; at 20 ℃; for 0.5h;

1,5-anhydro-2,3-di-O-benzyl-6-bromo-4-O-(methylsulfonyl)-D-glucitol; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; for 17h; Heating;
DOI:10.1021/jo0507901

Reference yield:

: 869194-05-8
1,5-anhydro-2,3-di-O-benzyl-4,6-di-O-(methylsulfonyl)-D-glucitol

: 869194-07-0
2-((2R,3R,4R,5S)-4,5-Bis-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-ylmethyl)-2-tert-butoxycarbonylamino-malonic acid diethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / NaBr; TBAB / dimethylsulfoxide / 12 h / 60 °C

2.1: NaH / toluene / 0.5 h / 20 °C

2.2: 56 percent / TBAI / tetrahydrofuran / 17 h / Heating

With tetrabutylammomium bromide; sodium hydride; sodium bromide; In dimethyl sulfoxide; toluene;
DOI:10.1021/jo0507901

Reference yield:

: 176168-90-4
1-anhydro-2,3-bis-O-benzyl-α-D-glucopyranoside

: 869194-07-0
2-((2R,3R,4R,5S)-4,5-Bis-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-ylmethyl)-2-tert-butoxycarbonylamino-malonic acid diethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / pyridine / CH₂Cl₂ / 12 h

2.1: 93 percent / NaBr; TBAB / dimethylsulfoxide / 12 h / 60 °C

3.1: NaH / toluene / 0.5 h / 20 °C

3.2: 56 percent / TBAI / tetrahydrofuran / 17 h / Heating

With pyridine; tetrabutylammomium bromide; sodium hydride; sodium bromide; In dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/jo0507901